臺灣博碩士論文加值系統

本研究利用1-indanone、氰基乙酸乙酯合成Ethyl(1-indanylidene)-cyanoanetate (3)，再與硫粉進行環化反應得到Ethyl-2-amino-8H-Indanone [2,1-b]thiophanone-3–carboxylate(5)。並用Ethyl-2-amino-8H-Indanone [2,1-b]thiophanone-3–carboxylate(5)當中間體在醋酸酐中反應得到Ethyl 2–acetyl-8H-indanone[2,1-b]thiophene -3 -carboxylate(7)然後與含醛基化合物得到azo-methine(C=N)(9)及methine(C=C)(10)、(11)化合物。
所有合成之化合物經光譜分析(UV、IR、1H-NMR及MS等)來確定結構。並分別在不同溶劑下測定其紫外/可見光吸收光譜，探討不同極性對最大吸收波長之影響。
關鍵字: 1-Indanone、醛類、次甲基

In this study, ethyl(1-indanylidene)-cyanoacetate(3) has been synthesized by the reaction of 1-indanone with Ethylcyanoacetate, followed by the cyclization with sulfur to given ethyl–2–amino– 8H-indanone[2,1-b]thiophanone-3–carboxylate(5).
Compound(5) reacted with acetic anhydride to yield ethyl 2–acetyl-8H-indanone[2,1-b]thiophene-3-carboxylate(7)and with aldehy- des to yield azomethine dyes (C=N) (9) and methine dye(10) and (11), respectively.
These compounds were determined by elemental and spectral analysis(FT-IR、1H-NMR and Mass). The solvatochromic behavior of these azo-methine dyes in various solvents were evaluated.
Keyword: 1-Indanone、aldehyde、methine

目 錄
摘 要......................................................I
ABSTRACT..................................................II
誌 謝.....................................................III
目 錄.....................................................IV
圖表索引..................................................VI
一、緒論 前言及研究目的…………………………………………………1
二、實驗部份..................................................................................2
2-1 實驗藥品..........................................2
2-2 實驗儀器 .........................................4
2-3 紫外線-可見光吸收光譜測定(UV).................................................5
2-4 熔點之測試........................................................................................................6
2-5 紅外線吸收光譜測試........................................................................................6
2-6 實驗方法.............................................................................................................7
2-6-1 中間體(3)、(5)及(7)之合成.............................................................................7
2-6-1-1 Ethyl(1-indanylidene)-cyanoanetate (3)…..................................................7
2-6-1-2 Ethyl 2-amino-8H –Indanone [2,1,b]thiophanone -3- carboxylate(5)..........7
2-6-1-3 Ethyl 2- acetyl -8H –Indane [2,1-b] thiophan one-3- carboxylate (7)..........8
2-6-2 染料(9a~9c)之合成..........................................................................................9
2-6-2-1 Ethyl 2-yl﹛(4-Dimethyl-amino-phenylimino)–indane[2,1-b]thiop- he-ne-3-carbozylate﹜-acetylonitrile(9a)……...................................9
2-6-2-2 Ethyl 2-yl﹛(4-nito–phenylimino)-indane[2,1-b]thiophene–3–carbozylate
﹜-acetylonitrile (9b)......................................................9
2-6-2-3 Ethyl 2-yl﹛(4-cyano–phenylimino)-indane[2,1-b]thiophene–3–carbozyla -te﹜-acetylonitrile (9c)...................................................10
2-6-3 染料(10a~10d)之合成............................................................................12
2-6-3-1 Ethyl 2-amino﹛(11-(4-nitro-phenyl)–indanone[2,1-b]thiophene-3-carbo- xylate﹜-acetonitrile (10a) ......................................................................12
2-6-3-2 Ethyl 2-amino﹛(11-(4-cyano-phenyl)–indanone[2,1-b]thiophene-3-carb- oxylate﹜-acetonitrile (10b) ….................................................................15
2-6-3-3 Ethyl 2-amino﹛(11-(4-chloro-phenyl)–indanone[2,1-b]thiophene-3- carboxylate﹜-acetonitrile (10c) .............................................................16
2-6-3-4 Ethyl2-amino﹛11-furan–2-yl-indanone[2,1-b]thiophene-3-carboxylate﹜-acetonitrile (10d)....................................................................................17
2-6-4 染料(11a~11b)之合成……............................................................................18
2-6-4-1 Ethyl 2-amino﹛(11-(4-dimethylamino-phenyl)–indanone[2,1-b]thiophene -3-carboxylate﹜-acetonitrile (11a) ........................................................18
2-6-4-2 Ethyl 2-amino﹛11-thiophen–2-yl-indanone[2,1-b]thiophene-3-carboxyla- te﹜-acetonitrile (11b).............................................................................19
三、結果與討論..........................................................................................................20
3-1 中間體3之合成...............................................................................................20
3-1-1 中間體3之物理實驗據...........................................................................21
3-1-2 中間體 3 之光譜數據分析.....................................................................22
3-2 中間體5之合成...............................................................................................24
3-2-1 中間體5之物理實驗數據........................................................................25
3-2-2 中間體5之光譜數據分析........................................................................26
3-3 中間體7之合成...............................................................................................28
3-3-1 中間體7之物理實驗數據.......................................................................29
3-3-2 中間體7之光譜數據分析........................................................................30
3-4 染料9a~9c之合成............................................................................................32
3-4-1 染料9a~9c之物理實驗數據....................................................................33
3-4-2 染料9a~9c之光譜數據分析....................................................................34
3-5 染料10a~10d之合成........................................................................................37
3-5-1 染料10a方法二之合成............................................................................38
3-5-2 染料10a~10d之物理實驗數據................................................................39
3-5-3 染料10a~10d之光譜數據分析................................................................40
3-6 染料11a~11b之合成........................................................................................44
3-6-1 染料11a~11b之物理實驗數據................................................................45
3-6-2 染料11a~11b之光譜數據分析................................................................46
3-7 染料9a~9c、10a~10d及 11a、11b的UV光譜數據分析............................48
3-7-1 染料9a~9c UV光譜數據分析..................................................................48
3-7-2 染料10a~10d 與11a、11bUV光譜數據分析.........................................51
四、 結論...................................................................................................................55
參考文獻......................................................................................................................58

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